Mack slept in the back of the Impala, Skittles clutched to her chest as usual as they sped down a dark road in the middle of the night. Ruby had shown up and told them about a girl named Anna Milton who escaped from a locked ward the previous day. Apparently, some really important demons were after her and the order was to capture her alive. They just didn't know why.

"Can I get a copy of the missing persons report?" Sam spoke into his phone. "Great. Okay. Thanks." He hung up. "Well, Anna Milton's definitely real." Dean scowled, white knuckling the steering wheel as he stared out at the road. "Doesn't mean the case is real. And this hospital's a three-day drive." Sam gave him a look. "We've driven further for less, Dean." The elder Winchester just shook his head, getting a rise out of Sam. "You got something to say, say it."

"Oh, I'm saying it- this sucks," Dean said, shooting a glare over at Sam. "You're not pissed we're going after the girl. You're pissed Ruby threw us the tip."

"Right. 'Cause as far as you're concerned, the Hell-bitch is practically family," Dean instigated the argument. "Yeah, boy, something major must've happened while I was downstairs, 'cause I come back, and- and you're BFF with a demon?"

"I told you, Dean, she helped me go after Lilith," Sam reminded him. "Well, thanks for the thumbnail- real vivid. You want to fill in a little detail?"

"Sure, Dean, let's trade stories. You first. How was Hell? Don't spare the details." Dean's expression soured, adjusting his grip even tighter on the wheel and glaring pointedly out the front windshield. While he had gotten a visit from Castiel at the park, Uriel had apparently shown up in the motel room with Sam and had told him to ask what Dean remembered from Hell. During their last hunt, where they dealt with a magic coin that had made a wishing well grant everybody's wishes, he had admitted to Sam that, yes, he did remember Hell, but, no, he wasn't going to talk about it.

"Of course I want to help however I can," the psychologist told them. They'd arrived at the hospital finally and were getting the rundown of how Anna had escaped. Sam and Dean were both dressed in their FBI threads and Mack was holding Dean's hand as they walked through the halls. "Now, the orderly has no recollection of Anna's escape?" Sam asked. "Apparently she knocked him unconscious. The blow caused some amnesia. He doesn't even remember going into her room."

The brothers exchanged a glance. "That's a hell of a right hook to knock out a guy that's got eighty pounds on her," Dean commented. "We think she may have planned this, waited behind the door," the doctor explained. "Right, uh, you mentioned Anna's illness was recent."

"Two months ago, she was happy, well-adjusted, journalism major, lots of friends- bright future," the psychologist confirmed. "So, what happened- she just... flipped?" Dean raised an eyebrow. "Well, that's the tragedy with schizophrenia. Within weeks Anna was overtaken by delusions."

"What kind of delusions?"

"She thought there were demons everywhere." The doctor handed Sam a sketchbook. "Interesting," Dean mused as Sam flipped open the book. "It's not uncommon for our patients to believe that monsters are real."

"Well that- that's just batty." As Sam turned the pages of the sketchbook, they found a few meaningful sketches accompanied by the words 'raising of the witnesses' and the next page 'Samhain, the next seal is broken.' The sketch of the witnesses had a picture of the brand that had been on the ghosts while the one of Samhain contained several jack-o'-lanterns and the mausoleum among other things. "That's Revelation," Dean said.

"Since when does the Book of Revelation have jack-o'-lanterns?" the psychologist asked, confused. "It's a, uh, it's a little-known translation," Dean covered quickly. "Well, Anna's father was a church deacon. When she became ill, her paranoia took on religious overtones. She was convinced the devil was about to rise up and end the world. I hope you find her. It's dangerous for her to be alone right now."

Thanking the doctor for his time, the Winchesters left to go check out the Milton house and talk to Anna's parents. When they arrived, no one answered, but the door had been left unlocked. "Mr. and Mrs. Milton?" Dean called out hesitantly. "We're from the sheriff's department. We just wanted to ask you a few questions," Sam added. They rounded the corner, finding the two dead bodies of Anna's parents, throats cut. Dean immediately grabbed Mack, burying her face in his neck so she wouldn't see.

Sam crept closer to the bodies, touching a yellow powder on the floor. "Sulfur," he noted. "The demons beat us here. Whatever the deal is with this Anna girl-"

"Yeah, they want her," Dean agreed. "They're not screwing around. Alright, so I'm 'Girl Interrupted' and I know the score of the apocalypse, just busted out of the nut-box... Possibly using superpowers, by the way. Where do I go?" Sam straightened up, walking over to some family photos and picking one up. He took out Anna's notebook, flipping through it until he found a motif of a stained glass window drawn a few times.

"Check this out," he said, holding the family photo up next to the sketches. The window in the notebook and the window on the church in the background of the photo were identical. "She was drawing the window of her church."

"Over and over," Sam nodded. "If you were religious, scared, and had demons on your ass, where would you go to feel safe?"

Sam, Dean and Mack crept into the attic at the church, the two elder Winchesters holding guns at the ready. Sam spotted someone hiding before Dean did. "Dean," he gestured with his gun. "Anna?" They put their guns away. "We're not gonna hurt you. We're here to help. My name is Sam. This is my brother Dean, and his daughter, Mckinley."

"Sam?" Anna asked, creeping out of her hiding spot. "Not Sam Winchester." Sam swallowed, glancing over at Dean. "Uh, yeah," he confirmed. "And you're Dean. The Dean?" Anna asked. Dean looked torn somewhere between being confused and extremely flattered. "Well, yeah. The Dean, I guess." Anna seemed to relax, smiling. She was a pretty girl, with long red hair and big green eyes. "It's really you. Oh, my God. The angels talk about you. You were in Hell, but Castiel pulled out, and some of them think you can help save us."

She looked back at Sam. "And some of them don't like you at all. They talk about you all the time lately. I feel like I know you." Dean furrowed his brow. "So, you talk to angels?" He didn't think that that was possible, but hadn't Castiel said when they first met that there were certain people who could perceive an angel's true form? Maybe Anna was like that. "Oh, no," Anna shook her head. "No, no way. Um, they probably don't even know I exist. I just kind of... overhear them."

"You overhear them?" Sam echoed. "Yeah, they talk, and sometimes I just... hear them in my head."

"Like... right now?"

"Not right this second, but a lot. And I can't shut them out, there are so many of them."

"So, they lock you up with a case of the crazies when really you were just... tuning in to angel radio?" Dean asked, trying to understand. Anna smiled at his words, looking relieved. "Yes. Thank you," she told him. He hadn't really meant it that way, but if it made her better, then he wasn't about to complain. "Anna when did the voices start?" Sam asked her curiously. "Do you remember?"

"I can tell you exactly- September 18th." Dean glanced over at Sam. "The day I got out of Hell." Anna nodded. "First words I heard, clear as a bell- 'Dean Winchester is saved.'" Not knowing what to make of it, Dean turned to Sam. "What do you think?"

"It's above my pay grade, man," Sam shrugged. Dean groaned internally- his thoughts exactly. He looked back at Anna, who was staring right back at him. "Well, at least now we know why the demons want you so bad. They get a hold of you, they can hear everything the other side's cooking. You're 1-900-angel." She didn't look too happy about that idea, and he didn't blame her. "Hey, um, do you know- are my parents okay? I- I didn't go home. I was afraid."

They were saved from answering as Ruby rushed into the room. "You got the girl. Good, let's go." Anna was staring at Ruby in horror, backing up several steps. "Her face!" Sam immediately tried to mediate the situation, "It's okay. She's here to help." Dean rolled his eyes, grumbling, "Yeah, don't be so sure."

"We have to hurry," Ruby informed them, ignoring everything that had just been said. "Why?" Dean asked suspiciously. "Because a demon's coming- big timer. We can fight later, Dean." Dean glared at her, getting angry. "Well, that's pretty convenient- showing up right when we find the girl with some bigwig on your tail?"

"I didn't bring him here, you did," she snapped.

"What?"

"He followed you from the girl's house. We got to go now."

"Dean," Sam interrupted. They all looked over as he pointed at a statue of the virgin Mary. It had started bleeding from its eyes. "It's too late," Ruby shook her head. "He's here." Sam hid both Anna and Mack in a nearby closet. "Okay. Stay in there. Don't move," he instructed. "Okay," Anna nodded. He shut them in, Anna holding Mack close in a comforting gesture, and then pulled out a flask of holy water.

"No, Sam, you got to pull him out right away." Dean reacted, not liking that idea at all. "Whoa, hold on a sec." Ruby glared back at him. "Now's not the time to bellyache about Sam going darkside. He does his thing, he exorcises that demon, or we die." Dean remained angry as Sam put the holy water back in his jacket. When the demon entered the attic, he tried to exorcise him, but it didn't work.

"That tickles," the demon grinned. "You don't have the juice to take me on, Sam." He threw Sam down the stairs. Dean took a turn, attacking with the demon knife, but was easily overtaken. "Hello again, Dean." Over at the closet, Anna screamed as Ruby pulled her and Mack out. "Come on, Dean. Don't you recognize me? Oh, I forgot- I'm wearing a pediatrician. But we were so close... in Hell." Dean's eyes widened in realization. "Alastair." Sam stabbed Alastair in the back with Ruby's knife, but barely missed his heart and instead only managed to bury it in his shoulder.

"You're gonna have to try a lot harder than that, son," Alastair sneered. Sam grabbed Dean and they looked over at the stained glass window from Anna's drawings. As the demon pulled the knife from his shoulder, they jumped through the window.

Dean was pissed. His shoulder was dislocated, his whole body was sore, and his daughter was missing along with Ruby and Anna. Sam was sewing up a cut on his own arm in the main area of their motel room while Dean used his good arm to splash water on his face in the bathroom. "Are you almost done?" he called out in a half-growl. "I'm going as fast as I can," Sam shot back. "Good, 'cause you know I got a dislocated shoulder over here." After wiping off his face, he grabbed a bottle of whiskey, taking a deep sip from it.

"Yeah, I'll pop it back when I'm finished," Sam replied, sticking his tongue through his teeth in concentration. "Gimme that." He swiped the bottle of whiskey from Dean, pouring it over his wound. "So, you lost the magic knife, huh?"

"Yeah, saving your ass. Who the hell was that demon?"

"No one good," Dean grimaced. "We got to find Mack and Anna." He was going to murder Ruby if Mack was hurt when they found them. It didn't matter that they didn't have the knife any more, he'd find a way. "Ruby's got them," Sam said, not making him feel better. "I'm sure they're okay. Alright. Come on. On three. One..." He popped Dean's shoulder back in place jarringly, not bothering to finish the countdown. Dean hissed, rotating the shoulder a few times to get feeling back in his arm.

"You sure about Ruby? 'Cause I think it's just as likely she used us to find radio girl and then brought that demon in to kill us. And now she's got Mack."

"No, she took them to keep them safe," Sam corrected. The words just reminded Dean that Castiel had done pretty much the exact same thing two months ago, taking Mack away to keep her safe. Although he'd had reservations then, too, he had at least felt a little better about that than having Sam's Hell-bitch do the same thing. Castiel had taken the time to give him a warning he was taking Mack where Ruby had just taken her. "Yeah. Well, why hasn't she called to tell us where she is, then?" he growled.

"Because that demon is probably watching us right now, waiting to follow us right back to Anna again. That's why he let us go." Dean couldn't believe what he was hearing. "You call this letting us go?"

"Yeah, I do. Look, killing us would've been no problem to that thing. That's why, for now, we just gotta lay low and wait for Ruby to contact us," Sam reasoned. "How's she gonna do that?" Dean snapped, pausing. "Why do you trust her so much?" His brother sighed, rolling his eyes. "I told you." Dean shook his head. "You got to do better than that. Hey, I'm not trying to pick a fight here. I mean, I really want to understand. But I need to know more. I deserve to know more."

"Because... she saved my life."

Six Months Earlier

Sam entered his motel room, completely wasted. As soon as the door closed, he was attacked by a man and a woman. They easily overpowered him in his drunken state. The woman took Ruby's knife from him while the man held him in place. "Thanks for keeping this warm for me, Sam," she grinned at him. "Ruby," he slurred. "It's nice to be back. Where I was, even for Hell, it was nasty. I guess I really pissed Lilith off. Imagine my relief when she gave me one last chance to take it topside. And all I had to do was find you and kill you."

Sam processed the words slowly, and when his inebriated mind finally caught up, he made no effort to fight. He was ready to die. None of the demons he'd summoned would trade his life for Dean's, and he couldn't take it anymore. "Fine," he told her. "Go ahead! Do it." She raised the knife, but instead of stabbing Sam, she stabbed the male demon. "Grab your keys. We got to go. Now!" Despite the amount of alcohol he'd consumed, Sam drove the Impala while Ruby rode shotgun.

"You know what sounds good?" she asked. "French fries. I'm starving. I just escaped Hell. I deserve a treat. You know, a 'thank you' would be nice." He glared over at her. "Who asked for your help?" Ruby sighed, rolling her eyes at him. "You have no idea what I've been through. When Lilith gets pissed, she gets creative. You want to hear about the corners of Hell I've seen, Sam?" His mind and body immediately rejected the idea. He had no interest in hearing about the place where his brother was currently residing. "No, I don't."

"And the things I had to do to convince her I was sorry?" Ruby continued on. "That I could be trusted?" Sam gave her another hard look. "Well, this will definitely get you a fat Christmas bonus." The demoness let out a single humorless laugh. "Very funny. I'm a fugitive... For you, Sam. I took all this risk to get back to you, so, yeah, I deserve a damn 'thank you.'"

"Who asked you to save me?"

"I'm just trying to help."

"Can you help me save Dean?"

"No. Nothing I know of is powerful enough to do that." He pulled the car to the side of the road, stopping. "Then I have no use for you," he spat. "What?" Ruby looked over at him incredulously. "Get out," he ordered. "Sam."

"Whose body are you riding, Ruby?" he asked her suddenly, not entirely sure why he thought to ask. "Why do you care? You've never asked me that before," she pointed out the obvious. He didn't know why he cared, he just knew that, "I'm asking now." She studied him, long and hard, before answering. "Some secretary."

"Let her go."

"Sam..."

"Or I send you right back to Hell."

After getting settled in an abandoned house, Sam began cleaning out his weapons. He was slightly less drunk, but still not totally sober. He couldn't remember the last time he was totally sober; sometime before Dean died. As he worked, there was a knock at the door. Grabbing a shotgun, he went over and answered it. A pretty brunette woman pushed past him inside, shoving a piece of paper at him as she went.

"Proof. This body is one hundred percent socially conscious. I recycle. Al Gore would be proud." Sam gaped at the paper in his hand, then looked up at the woman- Ruby in a new body. "You grabbed a coma patient?" She nodded, elaborating. "You didn't want me to take a body with someone in it, and I made sure the spirit was gone. Apartment was empty. You happy?" He continued to gawk at her, trying to understand what was happening. "Why are you here?"

"I can't bring Dean back. But I can get you something else you want," she informed him. "And, uh... what's that?" he swallowed suspiciously. "Lilith." Ruby let that hang in the air for a moment, and he realized what going after Lilith would mean. "You want me to use my psychic whatever."

"Look, I know that is spooks you-"

"Skip the speech. I'm ready. Let's go." She seemed amused at his eagerness, smirking at him. "Slow down there, cowboy." Sam wasn't having it, just wanting to know how he could become more powerful so he could take down Lilith. "Just tell me what to do."

"Look, Lilith is one scary bitch. When I was in the pit, there was talk. She's cooking up something big- apocalyptic big."

"So, let's kill her."

"You want to go in there and half-ass it like before? We have the time to get it right. Let's get it right." Sam considered this, thinking about how Ruby had wanted him to use his psychic abilities before, and it had been too late the night Dean went to Hell. "Okay," he relented. "What do you want from me?"

"Well, a little patience... and sobriety. Promise me that... and I will teach you everything I know."

Sam tried to exorcise the demon tied to a chair in front of him the way Ruby had shown him, but it wasn't working. Some black smoke started to come out of the demon's mouth before going back in. As Sam clutched his head in pain, the demon laughed and Ruby stabbed him with her knife. "Not funny," she snarled, then turned back to Sam. "Just give it time, Sam. It'll get better."

"What? I need more practice?" he snapped. Not for the first time since his forced sobriety, he wished he could just escape and drown himself in alcohol once more. No matter how hard he tried, he just couldn't seem to execute the things Ruby was teaching him correctly. She looked up at him with sympathy in her dark brown eyes. "I'm not talking about pulling demons. I know losing Dean was-"

"Hey! I don't want to talk about it. You know what? Where do you get off slapping me with that greeting-card, time-heals crap? What the hell do you know?" She moved in closer to him, a little frown tugging at the corner of her lips. "I used to be human. And I still remember what it's like to lose someone. I'm sorry." She put a hand on his shoulder, but Sam took a step back. "Unh-unh. Don't. I can't." She persisted, stepping in close once more. "Sam, you're not alone." Suddenly, her lips were on his, pressing in a gentle, not-quite-there kiss. He pushed her away, walking to the other side of the room.

"What are you doing?" he demanded, freaking out. "Sam, it's okay!" she insisted, attempting to get close to him again. "No, that is anything but okay!" His brain was in overdrive, reminding him that Ruby was a demon, and that this, what she was trying to do, was so wrong. "What's wrong?" Ruby asked, looking genuinely hurt that he was pushing her away. "What's wrong?" he echoed. "Where do I start?"

"Is it because of the body? Because I told you- it's all me inside of here. There is no one else. And it's nice inside this body, Sam. Soft and warm." He shook his head, warning bells still going off as she backed him against the couch. His legs hit the edge and buckled, forcing him to fall back, and she straddled his lap. "What are you doing?" he whispered. "Isn't it 'cause you're really scared to go there with a demon?" she purred, voice low in his ear. "Because it's wrong and it's bad and we shouldn't?"

He swallowed, watching as she pulled her shirt off, leaving her in just a bra. She kissed him, reaching down to undo his belt buckle. All thoughts left his head as she undid her own pants, and took him out of his underwear.

Present Day

"Sam?" Dean cut his brother off. Sam blinked, meeting his eyes. "Yeah?" he asked, taking in Dean's disgusted expression. "Too much information," Dean told him. "Hey, I told you I was coming clean," Sam defended himself, although he conceded Dean's point in his head. He had started to get a little carried away. Dean squirmed in his seat a little, looking away. "Yeah, but now I feel dirty. Okay, well, uh, brain stabbing imagery aside... So far all you've told me about is a manipulative bitch who, uh, screwed you, played mind games with you, and did everything in the book to get you to go bad."

"Yeah, well, there's more to the story."

"Just... skip the nudity, please," Dean begged him. Sam nodded, continuing on. "Pretty soon after... that..." he gestured with his hand, "I put together some signs... Omens."

"Saying what?"

"Lilith was in town. And I wanted to strike first."

Five Months Earlier

"You're not ready yet," Ruby argued with him. Sam was putting a duffel bag full of weapons together, determination set on his face. "It's now or never," he told her. "No, we got to wait until you get it right. You haven't been too successful." He waved her demon knife for her to see. "Alright, I'll use this."

"Stop. You can't just fly in there reckless, Sam. We need you to take this bitch out." Even though she had a point, he continued on anyway. "Oh, I'll take her out alright," he growled. "You get one shot, and you're it. You're the only one who can do it, Sam. So if she kills you first..."

"What?"

Ruby paused, as a thought struck her. "You don't want to survive this," she stated softly, eyes wide in realization. "Come on," Sam rolled his eyes, acting like the idea was absurd even though it was true. "It's a kamikaze attack," the demoness continued, voice getting stronger as she became more confident in the epiphany. "You want to die fighting Lilith."

"That's stupid," he lied, but she shook her head, not believing him. "No, it's the truth, because if you kill her and you survive this, then you have to go on without your brother! This isn't what Dean would have wanted! This isn't what he died for." Ruby ran in front of him, blocking his path out the door in an effort to stop him from leaving. "Get out of my way," he growled. "No, Sam! This is suicide!" Using the knife, he got her to move out of his way, then headed out the door.

He headed to the house where Lilith was supposedly staying, but instead found a scared human girl. "Please, I want to go home," she begged him. He paused, reminded of Mack, and two demons attacked him from behind. The knife flew out of his hand, skidding across the floor. "Lilith sends her regrets," one of the demons told him. "She couldn't make it."

Ruby grabbed the knife off the ground, killing one of the demons. "Take the girl and run!" she yelled at Sam, engaging the second demon in combat. He took the girl outside to the Impala, telling her to stay put and then hurried back inside. Ruby was being bested by the other demon, and Sam threw out a hand, using his powers to exorcise the demon with his mind. Blood trickled from his nose and he stumbled a bit once the demon was gone, leaning against a chair.

"Sam," Ruby said worriedly, hurrying to his side. "I'm okay, thanks," he assured her.

Present Day

Sam sighed, looking up at Dean with sad eyes. "Ruby came back for me. Whatever you have to say, she saved me. More than that, she got through to me. What she said to me... It's what you would have said. If it wasn't for her, I wouldn't be here." Dean was stunned at his brother's confession. He wasn't sure what to say as he processed it all. He opened his mouth to speak, but was interrupted by a knock at the door. "Housekeeping!"

"Not now!" Dean shouted. "Sir, I've got clean towels." Frustrated, Dean stood up, stomping over and wrenching open the door. The maid on the other side entered the room, shoving a stack of towels into his arms. "Couldn't you just leave 'em at the door?" he grumbled. The maid ignored him, going over to Sam and handing him a piece of paper. "I'm at this address," she told him. "I'm sorry, what?" Sam blinked, confused.

"Go now," the maid continued. "Go through the bathroom window, don't stop, don't take your car, don't pass go. There are demons in the hallway and in the parking lot." Sam gaped, realizing what was going on. "Ruby?" he asked. The maid- Ruby- put her hands on her hips and huffed. "Okay, yes, so I'm possessing this maid for a hot minute. Sue me."

"What about-"

"Coma girl? Slowly rotting on the floor back at the cabin with Anna and Mckinley, so I've got to hurry back. See you when you get there. Go!"